Take a self-guided walking tour of the Freedom Trail (for which we will provide a useful smartphone app). Alternatively we can always book you with an expert local guide, even one dressed in 18th century costume! This 2.5 mile route takes a couple of hours and weaves through the city past churches, parks and even a ship that played crucial roles in the foundation of the United States of America.

This afternoon you can relax in the city using our dossier again to engage in a spot of light shopping in Copley Square or Newbury Street's high-end boutiques. This evening it's time to try a different restaurant, maybe an authentic Italian (well, Italo-American) trattoria in North End or a dim sum dinner in Chinatown.

Explore the Harvard Museum of Natural History, walk along the Charles River spotting rowing eights training and admire the spires of the Memorial Hall before stopping for a delicious/heart attack inducing burger at famous institution Mr Bartley's Burgers.

This afternoon you can relax back in town before visiting Boston's other cathedral, otherwise known as Fenway Park ballpark, home of the legendary Red Sox baseball team. If they're playing at home, we can pre-purchase tickets for the game, but even if the Sox are on the road, you can still take a tour of the stadium and watch the game on TV with a beer in one of the stadium bars.

Leaving the city behind, you will journey up the coast through up-state Massachusetts, cutting across New Hampshire's small stretch of coastline and into Maine before arriving at the Inn by the Sea. The journey should take approximately two hours, dependent on how many times you stop to appreciate the views on the way.

On arrival, enjoy the charming coastal setting, just seven miles from the city of Portland. Also nearby (in fact a bracing hour and a half's walk away) is Maine's most famous lighthouse, at Portland Head, which was commissioned by George Washington in 1791. Whether you walk all the way there or just on the local beaches, the hotel has an excellent spa to relax weary limbs, and a restaurant serving New England classics.

After your stint in the city, a stay here on the coast is the chance to get your fill of some of the East Coast's freshest lobster, take long walks along beautiful beaches (the hotel itself sits pretty on a mile of pristine sand), and enjoy all manner of outdoorsy activities, from sailing to cycling.

It's about a four hour drive from Inn by the Sea to the heart of the so-called Green Mountain State if you take one of the scenic routes through New Hampshire (you should) past unspoilt woodland such as the White Mountain National Forest or beautiful bodies of water such as Lake Winnipesaukee. On arrival at your hotel any British visitor may - and not for the first time on this trip - have a certain sense of deja-vu, with English country house style and Scottish landscapes helping it all feel like an extremely comfortable home from home. We only work with a handful of the finest properties in Vermont, so wherever you end up staying, you will be able to stretch your legs on a lovely walk in stunning wooded surroundings before enjoying a delicious dinner using the region's fabled farm produce.

We can use the 'Fall Foliage Forecaster' to give a pretty good guess of when to be in the region, but even if you miss the full Fall colour palette, Vermont has a lot to offer from walking and cycling a range of well-marked trails to exploring the state's pretty as a picture towns. Keen foodies should note that Vermont is also at the forefront of the farm-to-fork movement so you can enjoy some mighty fine local produce from cheese to chocolate (and maple syrup, naturally) as well as a range of delicious craft ales from several award-winning microbreweries. As before, we'll take the hard work out of the decision-making process by providing a definitive list of the finest local producers and towns to visit.

The trip will probably take longer as there are plenty of places to stop en route as you head south along the valley of the Connecticut River before swinging south east through New Hampshire (always the bridesmaid, never the bride on this particular trip) and Massachusetts before reaching Rhode Island. Confusingly, the vast majority of the state isn't island at all, but a contiguous part of the New England coastline, but your eventual destination, Aquidneck Island, was once the eponymous Rhode Island. The island was also once the summer retreat of the robber baron billionaires (in today's money) of the Gilded Age, and you will stay in the main town of Newport at the Vanderbilt Grace, named - appropriately enough - after the foremost of the super-wealthy 19th and early 20th century industrialists. The hotel was once home to one of the famous Vanderbilt clan, so you can experience the sort of decadent comfort they once enjoyed.

We will create a driving or walking tour of a selection of the finest/showiest on the island, which range in style from French chateaux through to 'Jacobethan' English manor houses and Italian palazzos, all sharing one thing in common: a spectacularly conspicuous display of wealth. Back in Newport itself, explore the town's charming galleries and chic boutiques before lunch in one of many delicious seafood restaurants overlooking the harbour. The harbour is also the focal point of another phenomenon that has made Rhode Island famous - sailing. As the spiritual home of the America's Cup and host town to many other highly respected regattas, Newport prides itself on its maritime roots and we work with the best local companies to arrange private charters aboard anything from an elegant 80s schooner, to traditional sloop and an actual 60s America's Cup winning yacht. There's no better way to explore the waters off this beautiful island than under sail aboard a beautiful boat.

If you have longer to play with then we could create a longer itinerary involving stays on both of the islands, but with a more limited timeframe we'd recommend sticking to the mainland and Cape Cod itself, with day boat trips to the islands.

Stay at Chatham Bars Inn, a century old coastal retreat sitting right on the golden sands of Pleasant Bay (yes, it really is as quaint as it sounds). Spend the afternoon lazing on the beach, enjoying nature walks, cycling along the extensive Cape Cod Rail Trail or Province Lands Trail or visiting some of the startling modernist houses on the peninsula which contrast so beautifully with the wild surroundings and cutesy clapboard vernacular. Alternatively, retreat to the spa for complete relaxation.

If you choose Nantucket, then after breakfast head to Hyannis (a 40 minute drive) to catch the Nantucket high speed ferry, which leaves roughly every couple of hours, with the crossing taking an hour. Once on the island you can shop the preppy look (faded red trousers and boat shoes are seemingly obligatory), enjoy a lunch of local oysters and lobster rolls in one of several outstanding seafood restaurants (yes, yes, they're on the dossier) and learn more about how the community grew wealthy on the proceeds of the 19th century whaling trade in the Whaling Museum. Hear how neighbouring Martha's Vineyard was the location for Amity Island in the smash hit film Jaws, but Nantucket has its own mythical monster of the deep in Moby Dick, which was based on the true story of the Nantucket whaler Essex, sunk by a gigantic sperm whale in 1820. Take the fast ferry back to Hyannis and head back to Chatham, and if you can find the room to go again, there are yet more excellent restaurants in the vicinity, or at one of the hotel's own choices, including the pub-style Sacred Cod and STARS for delicious steaks.

Should you plump for former President Obama's favoured haunt of Martha's Vineyard, rather than embark from Hyannis, explore more of Cape Cod on the one and a quarter hour drive to Woods Hole, from where you can take the almost hourly ferry to Oak Bluffs on the island, which takes a mere 45 minutes. Once ashore, Jaws fans (which should be anyone who loves movies - discuss) will instantly recognise their surroundings, and can even enjoy a pint of Amity Ales in the Offshore Ale Company brewery and bar almost beside the ferry port. We don't advocate drinking and biking, but cycling is a lovely way to explore the island and we will recommend the best place to hire a bike in Oak Bluffs, which costs roughly £20 for the day. Cycling around the entire island, celeb spotting en route, would take about four hours, but factor in some beach time before returning to Oak Bluffs and taking the ferry back to Woods Hole. Then it's a drive back to the hotel for dinner.

Spend the day soaking up the sun and cycling the trails or head down the road to Hyannis and explore JFK's favourite place in America.

Enjoy your final morning in Cape Cod before lunch and hitting the road for the two hour drive back to Boston Logan International Airport. Drop off the car, check in and your flight will depart early evening.